Although less known than his theory of democracy, John Dewey’s social philosophy provides an articulate and original perspective on political life based on pragmatist intuitions. Dewey’s struggle with social philosophy spanned more than four decades of his intellectual life. This article provides an overview of the main themes that characterize it and shows that two distinct projects animate Dewey’s social philosophy. One is closer to the British reformist social philosophy of Jeremy Bentham and John S. Mill. Another is closer to the program of a critical theory of society initially developed by Karl Marx and subsequently expanded by the Frankfurt school. The article contends that to understand Dewey’s social philosophy we should first understand what he took and what he rejected from both these tradition, how he managed to steer a middle course between Mill and Marx.